If you smoked Colombian weed in the '70s and '80s, Tony Dokoupil would like to thank you: He says you paid for his swim lessons and kept him in the best private school in south Florida — at least for a little while.

Dokoupil's father started selling marijuana during the Nixon era, and expanded his operation until he became a partner in what his son describes as the biggest East Coast dope ring of the Reagan years, smuggling marijuana into the U.S.

But Dokoupil didn't know this until many years later, because his parents didn't tell him. His mother continued to keep the secret after his father disappeared from their lives, when Dokoupil was 10. When he did find out, he wanted to know the whole story. He combed through court documents and newspaper files and interviewed Drug Enforcement Administration agents who investigated the case, as well as more than a dozen smugglers and dealers, including his own father. He shares what he found in a new book called The Last Pirate: A Father, His Son and the Golden Age of Marijuana.

Dokoupil is a senior writer for NBC News. He has reported on the recent changes in marijuana laws, and the new entrepreneurs who are growing and selling marijuana. He tells Fresh Air's Terry Gross about his father's addiction to smuggling and how he ended up retiring.

Interview Highlights

On how he learned about his father's secret drug operation

I was pushing 30 by the time I found out. I had heard rumors that my family was involved in the business, but I thought it was typical hippie stuff. As far as I knew, my father sold real estate in Vermont and had an antique business. ... My mother told me that. That was the narrative. That's what I told other people's parents; that's what I told friends. And then I decided to do a background check on my father. ...

I called the National Archives, which is the keeper of 1 percent of all the paperwork that the federal government produces for all time — the most important things, the things they think historians will care about in the future. I said, "Do you happen to have a criminal record for this individual?" thinking I'd get nothing. Then I get an email with a faxed document inside it a couple weeks later. I click it open, and it's my father's indictment, 1986, for a single job in that year. He was busted for importing and distributing 35,000 pounds of marijuana, which is 17 tons. ... It was enough to roll a joint for every college-age person in America at that time. ... That was a single operation.

On the value of dealers during Richard Nixon's war on drugs

It creates the opportunity to be a hero. Use among his friends and among college kids is going through the roof. The government is trying to take it away; the kids want it; he can provide it.

Timothy Leary in 1969, in an article that was reprinted over and over again, called the drug dealer, the marijuana dealer, one of the three most significant figures of the era — as big as rock stars, as big as underground artists. And then ultimately, he concluded, bigger than both.

On his father's addiction to the thrill of smuggling

In the late 1970s, 90 percent of the marijuana was coming into Florida. It was primarily Colombian; some of it was Jamaican. My father's weed would be delivered to an old fishing shack in the [Florida] Keys. ... It's only one road that connects that necklace of islands and everyone knew that that was the road on which marijuana was smuggled into the country. So to smuggle on that road took an incredible amount of tolerance for risk.

So my father, despite being a partner in the operation, volunteered, for $25,000 a shot, to drive Winnebagos of weed out of the Keys and into America, just for the sheer thrill of it. He had no financial reason to do it. He had no operational reason to do it. ... But by then he was addicted to the sensation of it, to the risk.

On how his father left his family

My father retires. He has, at that point, $500,000 buried in a hillside in New Mexico; he's got a couple of coolers of money on Long Island. He has a safe deposit box with cash in it, plus he has the proceeds from his final job. He's essentially set for life. All he has to do is nothing and it proves to be the only thing he can't do.

He goes to St. Thomas [in the U.S. Virgin Islands] where they rent [a] long sailboat built for 49 people and party with just 12 on it: me and two other kids — smugglers' kids — my mother, one of his partner's girlfriends, an old partner. They have catered meals and tour the island and it's a retirement party. It's a celebration. ...

My father felt uncomfortable in those situations. He felt like he needed more. He needed to be different. So I have a memory of him leaving. We docked the boat, there are days still to come in the celebration, and he walks away. Memory is like surveillance footage: Everything gets picked up but you don't really review it unless there's an incident. So at the time it didn't occur to me that this was the last time I was going to see him in any kind of healthy condition. But in retrospect, that's the last time I saw him whole.

On how his father's downfall influenced his own sense of identity

Reporting this book and learning what I have about my father was confirming of my own sense of self. So, as someone raised primarily by my mother, I never recognized myself in her. She's wonderful. She's natively wise and accepting in these interesting ways, but she didn't have the same energy I had, she didn't really look like me, our interests didn't always align and I clearly came from some other stock.

My father was not the stock that I wanted to accept for a long time because my only impressions of him were negative. But once I saw what his career was like and how it aligned with the times and the excitement, and how good he was at it, I said, "Oh, OK. That is a nervous system I recognize, in fact."

I don't want to underplay the degree to which it was crushing to go through high school and college without clarity on where you came from and with a sense that your father was an empty vessel. ... The message that society pushes is "like father, like son." ... I felt that there was an inevitability that I would end up like him. ... I had to come to the realization that my father's destiny was one that he selected. ... Therefore, if he can make his life, I can make mine.

Copyright 2014 NPR. To see more, visit http://www.npr.org/.

Transcript

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. If you smoked Colombian weed in the 1970s and '80s, my guest, Tony Dokoupil, would like to thank you. He says you paid for his swim lessons and kept him in the best private school in South Florida, at least for a little while. His father was a marijuana dealer and smuggler. He started off selling marijuana during the Nixon era and expanded his operation until he became a partner in what Dokoupil describes as the biggest East Coast dope ring of the Reagan years, smuggling marijuana into the U.S.

But Dokoupil didn't know this until many years later because his parents didn't tell him. His mother continued to keep the secret after his father disappeared from their lives when Dokoupil was 10. When he did find out, he wanted to know the whole story. He combed through court documents and newspaper files and interviewed DEA agents who investigated the case, as well as more than a dozen smugglers and dealers, including his father.

Tony Dokoupil has written a new book called "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." He's currently a senior writer for NBC News and is a former senior reporter for Newsweek. He's reported on recent changes in marijuana laws and on the new entrepreneurs who are growing and selling marijuana.

Tony Dokoupil, welcome back to FRESH AIR. The last time we talked, it was so much about the issues. It's really good to have you back to talk about your life and your father's life. So I think the best way of getting the overview of your father's achievements in dealing and smuggling marijuana is to have you read from the opening chapter. Could you do that for us?

TONY DOKOUPIL: Absolutely. By his late 20s, my father sold bricks of Mexican reefer every weekend, sometimes from the window of a Good Humor ice cream truck. By the time he was 30, he moved hundreds of pounds a month in the trunk of an old Buick, crisscrossing the mid-Atlantic states under the guise of delivering concert tickets. We he (technical difficulties) enough money, he flew to Miami, uninvited and alone, to knock on the door of a former car mechanic who imported tons of Colombian marijuana.

He pitched himself as the most reliable black-marketeer on the East Coast, the best there is from box to box, drugs to cash. He drove mobile homes packed with weed out of Key West, secured a fleet of pickup trucks from New England and began to transport acres of South American Mountainside up the I-95 Reefer Express. This was late 1970s, I should add, which is also about the same time that he decided to start a family.

He became a father the year he graduated to loads of 10,000 and 20,000 pounds of marijuana, transported on freighters and tugboats, from the extreme northeastern edge of Colombia to sailboats near the Virgin Islands and ultimately to New York City wholesalers, vacation markets and college towns along the East Coast.

In the years that followed, he buried nearly a million dollars, invested more than a half-million more in a Yukon gold mine, and prepared the paperwork of escape should he ever had to hit reset as a card-carrying union welder and avid user of the Monmouth, New Jersey library system.

At his peak in the mid-1980s, which was also the peak of the drug war, an impossibly late date for pot smuggling, he broke a weeks-long national dope panic, a drought that New York Magazine dubbed reefer sadness. In a single load, he supplied enough marijuana to levitate every college-aged person in America and send them sideways to the store for snacks.

By that time, the old man, as he'd come to be called in the business, ran stateside operations for one of the most successful marijuana rings of the 20th century.

GROSS: Well, very impressive work for a marijuana smuggler. How old were you when you found out the scope of his operation?

DOKOUPIL: Geez, I was pushing 30 by the time I found out. I had heard rumors that my family was involved in the business, but I thought it was typical hippie stuff. As far as I knew, my father sold real estate in Vermont and had an antique business.

GROSS: Who told you that?

DOKOUPIL: They told me that. My mother told me that. That was the narrative. That's what I told other people's parents. That's what I told friends. And then I decided to do a background check on my father.

(LAUGHTER)

DOKOUPIL: I wasn't getting straight answers from him. I'd become a journalist. I knew how to do a court record search. First I did a local search just in Florida, things that had been digitized, and I found nothing of significance, and I sighed a little bit because I was kind of hoping. You know, he had been nothing of significance in my life, and in a funny way I wanted to discover that he had been a great smuggler.

GROSS: Yeah, I mean you hadn't seen him until - there was a long period of your life where he was totally absent, like from the age of 10 until you were an adult.

DOKOUPIL: My father - yeah, my father, the last contact we had was letters when I was 10, and it's not even clear to me that I read those letters. I think my mother kept them but never showed them to me. So for all intents and purposes there was more than 20 years in which he was - he wasn't in my life at all.

GROSS: So back to your background check.

(LAUGHTER)

DOKOUPIL: Yeah, so the background check. I called the National Archives, which is the keeper of one percent of all the paperwork that the federal government produces for all time, the most important things, the things that they think historians will care about in the future. And I said, do you happen to have a criminal record for this individual, thinking I'd get nothing.

And then I get an email with a faxed document inside of it a couple weeks later, and I click it open, and it's my father's indictment, 1986, for a single job in that year. He was busted for importing and distributing 35,000 pounds of marijuana, which is 17 tons, which if you think that a joint, a very thick joint, has about a gram of marijuana, you can roll millions and millions of joints in 35,000 pounds of marijuana.

It was enough to roll a joint for every college-aged person in America at that time, a huge amount.

GROSS: And that was one operation, or that was the sum of his operations?

DOKOUPIL: That was a single operation. He had been doing that every year for years at that point, for eight years at that scale. And the work, he'd begun selling pounds - keys, he called them - Mexican reefer was on the metric system, kilos in 1971. And so in 1986, this is 15 years later, it's the pinnacle of his career, and it's quite the pinnacle. I mean it's impressive.

So then I called my mother, and I said hey, I got this indictment from 1986. What do you know about that? And she's silent for a second, and then she says we were going to tell you.

GROSS: Eventually...

(LAUGHTER)

DOKOUPIL: We were going to tell you. We were going to tell you. And I said: When? And she said, well, right about now seemed right, but then you started getting that journalist bug, so we just let you find out.

GROSS: OK. My guest is Tony Dokoupil, and what he found out was that his father was a huge smuggler of marijuana, and his new book about his father is called "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana."

Early on in your father's career as a marijuana smuggler and dealer, he was dealing to rock bands, and you refer to this in your reading. He was - he had been like a ticket distributor, and in distributing tickets for rock concerts, correct me if I'm wrong here, he managed to also have contacts in bands. And he sold them marijuana.

DOKOUPIL: Absolutely. So one of the coolest jobs in America in the 1970s other than marijuana dealer was ticket seller, because you weren't the guy in the booth with alphabetized envelopes, you had an actual paper ticket that you had to drive around to clothing stores and radio stations and sandwich shops, and that's where people would actually buy their concert tickets.

And he would do that, making marijuana drops in addition to ticket drops. And then when the concert actually occurred, he would be there with the organizer, who was at the time the kingpin for that little area, my father was just starting out, and the smoke that filled the arena while the band Alabama was playing, you know, it would be their dope.

GROSS: So in talking about your father's work smuggling drugs, you talk about how the drug laws changed during that period, and you say in 1969, when Nixon took office, he started a war on drugs, and soon Congress passed the Controlled Substances Act. How did that change the law about marijuana?

DOKOUPIL: So marijuana famously was categorized as a Schedule One drug in 1970. Nixon was the one who did this. And it classed it in the same category as heroin, a drug with no medical value and with a high potential for abuse. So the very thing that was exploding in use among young people, greatest flouting of law since Prohibition, was the thing that he considered to be the most dangerous substance, among the most dangerous substances in the country.

So in 1970, Congress passed the Controlled Substances Act, and this was Richard Nixon's centerpiece effort to control drug use nationwide. And importantly, marijuana wasn't considered a small problem. It was considered a huge problem. It was Schedule One, and all the might of the federal government was used to try to push it out of the country.

GROSS: So, Nixon starts the war on drugs. How does that affect the early part of your father's life dealing and smuggling marijuana?

DOKOUPIL: It creates the opportunity to be a hero. Use among his friends and among college kids is going through the roof. The government is trying to take it away. The kids want it. He can provide it. Timothy Leary - 1969, in an article that was then reprinted over and over again, called the drug dealer, the marijuana dealer, one of the three most significant figures of the era, as big as rock stars, as big as underground artists and then ultimately he concluded bigger than both.

GROSS: In part because President Carter favored initially decriminalization of marijuana, your father was preparing for the decriminalization and possibly even legalization of marijuana. He didn't see that during his career. What was he doing to prepare? How did he change his operation?

DOKOUPIL: So my father might have gotten out of the business, and thus my life would be very, very different, in 1976, because the market for Mexican marijuana, which was his product, was falling apart. But at that same time, Jimmy Carter was running for office on a platform of decriminalizing marijuana. And then in 1977, he stood on the floor of Congress, and he said the penalties against drug use should in no case be more severe than the problems caused by the drug itself.

And so that is the golden - that is the golden hour of the golden era of marijuana. The president of the United States is saying we should soften drug laws. The advocates are saying this is going to be fully legal by 1980. That was the feeling in 1977. So my father, of course, was not going to drop out. He wasn't going to become a teacher. He was on the ground floor of something huge.

GROSS: So he could no longer deal Mexican marijuana. What had happened to the market from Mexico?

DOKOUPIL: Mexican marijuana was exciting at first, but by the late 1970s, there was a magazine called High Times that had been founded and spread, four million readers a month, and that magazine began to teach smokers about quality. You couldn't just have average marijuana grown on a mountainside in Mexico. You needed to have a particular potency. And not only that, you needed to have a story behind the weed.

When you rolled it at your party, you wanted to be able to say this came from an exotic locale, here's how it was processed, here's how it was packaged. Mexico didn't have a good story. Of course, you know, the Tourism Board will tell you that Mexico is plenty exotic, and it is. It has jungles and has ruins, and it has outlaw history.

But the people who read High Times and the editors of High Times started pushing Colombian. Colombian emerged as the great, sexy get. It's what you needed if you wanted to be a big-time dealer. And so my father needed to get Colombian, and so he did. And that was his trip to Miami in 1977. He, through sheer luck, his sister, my aunt, had moved to Miami to go to school, and she met a car mechanic who had only a motorcycle but a desire to sell marijuana.

So off the back of this motorcycle, he sold a single bale and did well enough to get another bale and another bale, and then he bought a van, and the operation got bigger and bigger. He ended up being a middleman between Cuban gangsters who were bringing Colombian dope to the Keys and then pushing it into wholesale markets in Louisiana and North Carolina.

And my father just went down and knocked on the door one day, uninvited, and believed, on sheer charisma, power of personality, he could talk his way into this guy's operation. And he did.

GROSS: If you're just joining us, my guest is Tony Dokoupil, and his new book "The Last Pirate" is about his father, who was a major marijuana smuggler in the 1970s and '80s. Let's take a short break here, and then we'll talk some more. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR, and if you're just joining us, my guest is Tony Dokoupil. We're talking about his new memoir "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." And it's about his father, whose name is also Tony Dokoupil, who was a major marijuana smuggler in the 1970s and '80s.

So your father starts smuggling marijuana from Colombia up the East Coast of the United States. Can you - what can you describe about that operation?

DOKOUPIL: In the late 1970s, 90 percent of the marijuana was coming into Florida. It was primarily Colombian, some of it was Jamaican. My father's weed would be delivered to an old fishing shack in the Keys. The Keys are this archipelago of islands off the coast of Florida. They arc toward Cancun, deep into the Caribbean. And it's only one road that connects that string of - that necklace of islands.

And everyone knew that that was the source of - that was the road on which marijuana was smuggled into the country. And so to smuggle on that road took an incredible amount of tolerance for risk. And my father, despite being, you know, a partner in the operation, volunteered for $25,000 a shot, to drive Winnebagos of weed out of the Keys and into America just for the sheer thrill of it.

He had no financial reason to do it. He had no operational reason to do it. Somebody else could've taken on that job. But by then he was addicted to the sensation of it, to the risk.

GROSS: And then he got even bigger in that operation, right, or created his own?

DOKOUPIL: Right, oh, he created his own. So by 1978, he had a reputation. He was not only moving tons out of Key West, but in his wholesale market in New York City and points north, he had become known as a reliable guy, as a guy who could sell quickly and then send a wave of money back down south, all the way to the islands, all the way to Colombia, all the way to the farmer on a hillside.

And so a bigger smuggler - the DEA says the biggest smuggler of the era, a man named Willy Terry, could get all the marijuana he needed out of south America, and he just needed somebody to sell it. He didn't like his old partner because his old partner had diversified into cocaine, and Willy, like my father, believed that cocaine was something you didn't want to get involved in. It was bad news to sell it.

Marijuana was freedom and joy, and cocaine was a soul killer. So he sought a partner who shared his values. And he yanked a chain of associations that led to my dad. My dad was that guy. And then from 1978 to '86, that's when the huge jobs started. It wasn't just - it wasn't just Winnebago loads, it was multiple sailboats with tons on it apiece, and my father was the guy there in the tall grass to receive it.

GROSS: And then ship it by what - up the East Coast?

DOKOUPIL: Oh he had two trucks. He had a fish truck, and he had a truck marked Global Moving, and he just cycled - he just recycled those. You know, they had a mechanic who's on staff, and they would - so, you know, for example you might have a drop point in Maryland where three sailboats would go. Both trucks would be there. They'd make a drop. They'd take it to the stash house, which was usually in Connecticut, and then go to the second drop point.

So three more sailboats would head further north, maybe go to Maine or Massachusetts, and the trucks by then would be able to beat them to the point, pick up the load and go to the stash house, and the load would be parceled out from there.

GROSS: So after your father - like how old were you when your father got out of the smuggling business and then started using a lot of drugs and bottoming out? He and your mother separate.

DOKOUPIL: I was six years old.

GROSS: OK.

DOKOUPIL: Yeah, I was six years old. My father retires. He has, at that point, $500,000 buried in a hillside in New Mexico. He's got a couple coolers of money on Long Island. He has a safe deposit box with cash in it. Plus he has the proceeds from his final job. He's essentially set for life. All he has to do is nothing, and it proves to be the only thing he can't do.

He goes to St. Thomas, where they rent a long sailboat built for 49 people and partied with just 12 on it, and me and two other kids, you know, smugglers' kids, my mother, one of his partner's girlfriend, an old partner, they have catered meals and tour the islands, and it's a retirement party. It's a celebration.

There are red snapper sandwiches and Carl Hiaasen novels and crab legs and wonderfully cut fruit, and it should just be a happy time. But my father felt uncomfortable in those situations. He felt like he needed more. He needed to be different. And so I have a memory of him leaving. We docked the boat. There are days still to come in the celebration, and he walks away.

And, you know, memory is like surveillance footage, everything gets picked up, but you don't really review it unless there's an incident, and so at the time it didn't occur to me that this was the last time I was going to see him in any kind of healthy condition. But in retrospect, that's the last time I saw him whole, I saw him, you know, with vigor at a kind of peak, and it was all downhill from there.

GROSS: And was that the last time you saw him for a long time, too?

DOKOUPIL: I saw him one other time - no, I saw him at a rehab facility a couple years later, maybe three years later, and we went fishing on a little manmade lake with those short fishing poles, those pathetic little things, and it was - it left me with the sensation that - it left me with the impression that my father was a failure.

I had no idea about the dealing, of course. I thought he was addict.

GROSS: He was an addict, but you had no idea about the dealing.

(LAUGHTER)

DOKOUPIL: Yeah.

GROSS: But he was an addict, yeah.

DOKOUPIL: Yeah, yeah, so, you know, I see him - so in my memory I have him walking away in 1986, and it's the last time I see him with a glow, you know, with health, with youth, with success, you know, with like the full flush of life. And then there are a few rehab moments after that, but until I'm adult, I don't see him.

GROSS: Tony Dokoupil will be back in the second half of the show. His new book is called "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross back with Tony Dokoupil, author of the new book "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." Dokoupil's father was a marijuana dealer and smuggler in the '70s and '80s. He became a partner in what Dokoupil describes as the biggest East Coast dupe ring of the Reagan years. His parents separated when he was young, and his father dropped out of sight when he was 10, after retiring from the business. It wasn't until Dokoupil was about 30 that he found out about his father's dealing and smuggling.

It's a really complicated, crazy story the way your father finally gets arrested for a 1986 smuggling operation, but he gets arrested for it several years later, in the early 1990s. And it's a complicated story. Let's try to make it really simple, which is going to be impossible, because the person who gives his name to the federal agents is actually not only your father's former partner, but the person who became your mother's boyfriend and then husband, your stepfather.

DOKOUPIL: I was the best man at the wedding. Yes.

GROSS: And, in fact, one of the reasons you say that your mother and stepfather were in love, but that one of the main reasons your mother married your stepfather was that so that she would be exempted from testifying against him. You don't have to testify against a spouse.

DOKOUPIL: Right. Everyone who's seen "Breaking Bad" knows that you can't be compelled to testify against your spouse. My father bought him out after '86, lost everything, ended up homeless. He was in love with romanticism, and so, of course, even in homelessness, he's living a romantic life. He's in - sleeping in lifeguard stands on Miami Beach.

And he begins to climb back up into some kind of mainstream existence. He gets a job cleaning the beach on Miami Beach in 1990. He's in - he's going to Narcotics Anonymous meetings. And at that time, as he's trying to make his way back toward me, back toward fatherhood, back toward normalcy, the, one of Reagan's taskforces, the New England Drug and Organized Crime Taskforce, is closing in on the ring that my father was part of.

It busts Willie Terry(ph), who was the smuggler extraordinaire in Portugal at that time. He went to Portugal to live the high life, but he couldn't, like my father, he was - continued to use, continue to live excessively, and he gets noticed as a white guy with a Ferrari in a resort town in Portugal. The Feds go to visit him. They bust him at the dentist. They put him in jail there, and they say if you cooperate, we can get you out and get you back home. So, he agrees. And the person that he turns along with him to make the case, to confirm what he's saying, is my stepfather.

And my - this was a difficult thing to discover in the reporting process. You know, according to my stepfather's close friends, my stepfather had a plan, and that plan was we know that your father has money buried. We know that the Feds don't know about it. If I cooperate, I can get immunity for myself. I could lock off your mother as a source of information, and we can dig up that cash. It can be ours. And who cares if big Tony goes to jail? And so that's what they did. It's crazy. (unintelligible)

GROSS: And they found the money that was buried, that it stashed?

DOKOUPIL: They did. Yeah. They went to New Mexico. My mother went with me in a Winnebago, because you can't take that kind of money on an airplane, and she dug it up. And, you know, my father claimed it was a half million, and I believe him. She claims it was about $375,000. And that's what they lived on in the years that followed. They didn't manage it particularly well.

And then after the cooperation with the Feds, my life gets cracked in half. So, up to that point, I'm living incredibly comfortably. I'm going to a fantastic private school. We're going on Caribbean vacations all the time. Everything I would want, I have. And then, suddenly, we don't have any money anymore, of significance. The money is petered away. And suddenly, instead of a rich kid, I'm being called poor boy. And, you know, I had to have two halves of a life, and those halves don't cohere. And it's incredibly disjointing and confusing. Yeah. It's - there was a lot of mystery that I had to - there was much - there were questions, big questions I had about how that could have happened, and I didn't know the answers to them until I reported this book.

GROSS: How has your identity, your personal identity been changed knowing that your father was a very successful drug smuggler before he became a very sick drug addict?

DOKOUPIL: I - reporting this book and learning what had happened with my father was confirming of my own sense of self. So, as my, as someone raised primarily by my mother, I never recognized myself in her. She's wonderful. She's natively wise and accepting in these interesting ways. But she didn't have the same energy I had. She didn't really look like me. Interests didn't always align, and I clearly came from some other stock.

And my father was not the stock I wanted to accept for a long time, because my only impressions of him were negative. But once I saw what his career was like and how it aligned with the times, and the excitement and how good he was at it, I saw oh, OK. That is a nervous system I recognize, in fact.

I don't want to underplay the degree in which it was crushing to go through high school and college without clarity on where you came from and with a sense that your father was an empty vessel. It was more than crushing. I mean, I walked a very fine line between living and dying in the years after college because I felt, you know, the message that society pushes is like father, like son. We say you can do anything with your life, but next to that we say, like father, like son.

And I bought into the idea of like father, like son. I felt that there was an inevitability that I would end up like him, and I wanted to give up on that. I wanted to end it before it happened. And so I did become very close to ending it. And now, having written this book, I'm capable of seeing - I had to come to the realization that my father's destiny was one that he selected. He had autonomy over it. He wanted it. He regrets none of it. And therefore, if he can make his life, I can make mine. I'm not - I don't have to be him. I can be - what I can inherit from him is the autonomy to be whatever I want.

GROSS: Is what made you most afraid of becoming like him, was it the fact that he seemed to be either schizophrenic or bipolar or both?

DOKOUPIL: OK. So, the mental health component of this is a tricky one, because, I mean, yes, that's a huge part of it. I felt like - but it's not only that. I felt like I didn't recognize myself in my mother, and he was my father, a bombed-out, mentally ill recovering addict. And I felt like that is - those are the synapses that I have firing right now. And so why don't I just skip ahead in the story? Why do I have to make it - fight against my nature?

GROSS: Were you having any symptoms then, or were you very depressed?

DOKOUPIL: Yeah. I had - I was very depressed in college. Yes. Definitely. I wasn't having symptoms of deeper mental illness, but I had more than average depression, and I tried - I did my best to fight it and, you know, was not particularly successful. But...

GROSS: I'm just wondering, and talk about your father's...

DOKOUPIL: Go ahead.

GROSS: ...need for risk. Do you think it was always prone to depression, and risk kind of got him out of that, because of all the adrenaline or whatever, or all the focus?

DOKOUPIL: I think my father is like a shark. A shark has to move, or it sinks. And he needed sensation, and in the absence of sensation, his mood sunk and his mind came apart. So, it was move or die for him, and I recognize that.

GROSS: In yourself?

DOKOUPIL: I recognize that in myself. Absolutely. And, you know, I would think that in a very fundamental way, I've merely found more healthy and societally acceptable expressions for the very same tendencies that he has, right. I probably have an addiction to work in a way he had an addiction to substances. I have an addiction to the thrill of a certain kind of success in my line of work. And it's chemically the same thing, but it's - it's neurochemically the same thing, but we view it differently.

GROSS: My guest is Tony Dokoupil. His new book is called "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." We'll talk more after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. My guest Tony Dokoupil is the author of the new book "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." His father was a marijuana dealer and smuggler in the '70s and '80s, and was a partner in what Dokoupil describes as the biggest East Coast dope ring of the Reagan years. His last big smuggle was in 1986, but he wasn't arrested until 1992.

So, your father was really very lucky in the respect that once he was sentenced, he was given a very relatively minimum sentence, because his - the operation that he was busted for was in 1986, and minimum mandatory sentencing didn't go into effect until after that, and it wasn't retroactive to crimes committed before. So, he was - he just managed to get by without a really long stay in prison.

DOKOUPIL: Yes. He just managed. He also cooperated, right? I would like to say my father was a standup pirate, but he was not. He was fully willing to share what he knew about other people in the business. I mean, he was kind of honorable. He didn't implicate my mother. He didn't try to, as far as I can tell. He didn't implicate some of his down-market dealers, and as a result, he wasn't prosecuted under the Continuing Criminal Enterprise statutes, which would have given him a much longer stay in prison. In fact, one of his partners was, and got 10 years. And so, you know, ultimately, you know, my father tried to live by this pirate code, and the biggest aspect of that code is that you don't you don't tell, and he told. He definitely told. I was...

GROSS: And he's not the only one, obviously. Yeah.

DOKOUPIL: He's not the only one. He's not the only one. I had this amazing interview with the former mayor of Las Vegas, who made his money as a lawyer for many reputed mobsters. And I was talking to him about how terrible things had gotten in Las Vegas during the recession. And I had the, you know, all the power in the interview was on my side of the table. And then we took this little detour into personal stuff, and he had heard about my father or read something I had written about it or said, and he asked how long my father went to jail. And I said, oh, he did about a year and a half in custody, in all. And then he points at me and he says: Your father's a rat.

(LAUGHTER)

DOKOUPIL: And I was like, yeah, yeah. That changed the dynamic of that interview.

GROSS: How has investigating your father's story - his story as a marijuana outlaw and also his story as a drug user - affected your - you might not want to answer this - but affected your personal use or abstinence from drugs?

DOKOUPIL: OK. So why am I not a drug addict is basically the question that people are often interested in. You have all of the risk factors, you know, absentee father, a history of abuse in the family, what - you know, how could you be upstanding? And I just got lucky in a very specific way. I can't handle liquor. I don't have the cauldron for it. I have a weak stomach. And if you - and that's important, because there was no - there's no way for me to consistently participate in a life of debauchery. As much as I would like to, on some really deep cellular level, I just can't do it. I feel sick. And, you know, the prerequisite for serious substance abuse is, you know, insides made of iron, and I don't have them. Pure luck.

GROSS: So, you have such a complicated relationship with your father. Do you see him now? Like, is he well now?

DOKOUPIL: No. My father is not particularly well. I do see him. He lives in Boston - he lives in Cambridge. You know, the theme in my father's life is romance, romance, romance. And, of course, now he's not just a bum living off government proceeds. He's a Harvard bum. So, he lives in public housing. He was never charged with tax fraud, so he gets Social Security that he paid as a dealer. And so he lives in public housing near Cambridge. He walks around on Harvard's campus. He got a loaner bike, an English country bike from the 1950s, you know, one of these gorgeous things that would be very hip in any major city, and he rides along the Charles River and he collapses in the grass and watches the girls run.

(LAUGHTER)

DOKOUPIL: And then when he gets tired, he goes to yoga at the senior center and gets a free sandwich. And, like, he's just - he's living a great life. But it's a pretty dented-up life. I was with him recently, and we were printing out some pictures of his grandkids. And the guy behind the counter, who knew my father - because it was a local shop - and he said, oh, your name is Tony, too.

And I said, yeah. I'm his son. And the guy goes, oh, I thought you were his lawyer.

(LAUGHTER)

DOKOUPIL: Oh, OK. So I guess we don't - we make an unusual pair. You know, he's - my father, he's got really - he's got scars on his face from blackouts and from a prison fight, and he looks like a guy who has been on the longest all-night bus trip in history, like he's just been sleeping upright in a greasy bus chair for the last 10 years. That is the level of health that he exudes. He projects sickness, basically.

GROSS: And...

DOKOUPIL: But a romantic kind of sickness.

GROSS: So your father walked out on you and your mother when you were 10. It was years before you saw him again and, you know, he did time in prison. He became a broken man and a drug addict. But he gave you this incredible legacy, which is not what he intended, I think, to give you - or certainly not what you expected to get - which is his story.

I mean, for a writer, his story isn't necessarily the story a son would want, but it's a story a writer could use. And you did. So does that...

DOKOUPIL: How do I feel about exploiting my father for personal gain? I feel fantastic about it, because I feel he participates in it.

GROSS: That wasn't going to be my question, but go ahead.

(LAUGHTER)

DOKOUPIL: Oh, no, no. I mean, you know, my father disinherited me one orgasm, one hit, one high rise hotel room at a time. And he knows this, and he feels bad about it. And he knows that he can repay me in some small way by taking me back through it, by including me. Right?

I was always in the dark, and now, in writing this book, there was a way in which he put his arm around my shoulder and opened a side door and took me into a world that I hadn't known existed. And it was a gift. And now, in telling the story, because I'm a writer, I get a personal gain, but I also - this is what I love to do.

So life could've turned out very differently, and there for a long time, I wished my father was just a guy who worked for IBM or the equivalent, but now I wouldn't have it any other way. So, ultimately, having come out of the other end of a terrible tunnel, I feel a strange kind of gratefulness, and I can admit that I'm partially proud of my father and I'm happy that he's my dad.

GROSS: Tony Dokoupil, thank you so much for talking with us.

DOKOUPIL: Thanks a lot for having me.

GROSS: Tony Dokoupil's new book is called "The Last Pirate: A Father, His Son, and the Golden Age of Marijuana." You can read an excerpt on our website: freshair.npr.org. I would bet that a lot of people who were getting high on the marijuana that Dokoupil's father smuggled into the U.S. in the '70s and '80s were smoking it at Grateful Dead concerts.

A Dead concert from 40 years ago has just been released for the first time. Critic Milo Miles was at that concert, and will have a review after we take a short break. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.